Hydrochloric Acid → 5-Nitronaphthalene-1,4-dione

Participants

Reaction Conditions

Reaction Steps

5.5 g (0.025 mol) of 8-nitro-1,4-naphthoquinone-1-oxime and 21 g (0.11 mol) of iron (II) chloride tetrahydrate are heated to reflux temperature in 100 ml of methyl ethyl ketone. 25 g of hydrogen chloride gas are then introduced over a period of 20 minutes during which the sump temperature is kept at 87° to 90°C. The reaction mixture is stirred for another hour at this temperature, after which it is poured into 1000 ml of water heated to approximately 50°C, followed by stirring for 30 minutes at that temperature. The reaction product precipitated is then filtered off under suction. Recrystallization from toluene following the addition of 2 g of active carbon gives 4 g (78 percent of the theoretical yield) of 5-nitro-1,4-naphthoquinone melting at 164°C.

Provenance & Evidence